How to Confront a Difficult Boss the Right Way

How to Confront a Difficult Boss the Right Way
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Tough Situations

As both an employee and a business owner throughout my career, I’ve found myself in some sticky situations when it comes to decisions made by the boss and what I feel is really the correct solution. So, how do you confront a difficult boss without losing their respect or your job?

Although I can’t offer up every situation where you need to speak up and claim your space, I think the following tips will help when it’s time for you to stand up and take charge.

You’re Fired!

Donald Trump

Donald Trump of the Celebrity Apprentice may love his trademark phrase, “you’re fired,” but it’s not something most of us want to hear, especially when defending our opinions or ideas. The following include some situations you may relate to—the best advice for every situation is to stay calm.

Disciplinary – Let’s say the boss says you’re late all the time, miss too much work and he writes you up offering you just “one more chance.” In reality, however, you’ve only missed one day in six months and you’ve only been late once in the same period! Bosses are famous for wanting to be king of the mountain and love letting you know it. That doesn’t mean they are correct. For example, what if that one day you missed in six months was followed by a family funeral where you took advantage of your allowed leave? He’s most likely angry not only because of the missed day, but your benefit days off. Even if this isn’t fair, ask to meet with him and bring your timesheets along to show how you really have been following company policy on absenteeism and tardiness.

Inaccurate Pay – So you’re promised overtime, work overtime but when the paycheck comes along you’ve only been paid for regular hours worked—not the overtime. If you have an HR or personnel department, start there first. If not, it’s the employer’s legal obligation to pay you for overtime. Instead of barging in and demanding immediate payment, grab the employee handbook and highlight the section that discusses overtime pay. Present your case in a calm manner reminding the boss of company rules, but don’t threaten to sue.

Wrong Decisions – You’re working on a project for one of the company’s clients and the boss suddenly decides he doesn’t like your progress or decision making and threatens to give the task to someone else. If you are sure your way is the best way, ask for a meeting and bring along project information, progress and expected results based upon the client’s wishes. If you can show the boss you are doing what the client asked for, most likely you’ll win the argument. If a supervisor is the problem and you just can’t win the argument, speak to their supervisor and explain your problem.

No Life – If your boss demands all of your time—even when not at the office, it’s time to let them know. I once had a boss who called the house in the evenings on a consistent basis. The best way to end this if you have a partner is to let the partner answer the phone and tell them you’re unavailable. (My husband actually told the boss “she’s yours from 8:00 to 6:00 okay?”) If you’re single, let the answering machine pick up the call and explain to your boss why you can’t be on constant call and you need downtime as much as he or she does.

Just Plain Mean

Is Your Boss Mean

Unfortunately, some bosses are just plain mean. This is not a personality issue alone and most of the time the boss is mad at low income and high expenses. Maybe a loan or a credit request was turned down or maybe a bid didn’t go as planned. Whatever the reason, some in charge simply can’t separate the bad and spread fire through the office. Below are some instances you may face.

Company Worries – If your leader is worried about the company—for whatever reason—that’s not really, nor should it be, your concern. A boss should avoid picking on employees because of a bad mood but often they do. This is a little tougher to handle. Instead of going it alone, find some support. By support, I mean a supervisor or co-worker that can help you confront a difficult boss. Prepare ahead of time what you want to say and ask the second party to also offer information showing the boss is being unfair or angry for no reason.

Legal Concerns – If you feel you are the victim of any type of discrimination or sexual harassment and have reported the same to no avail, no matter how you feel about your boss, if they aren’t willing to help you, report the incident to the Equal Employment Opportunity Commission (EEOC). While filing a formal complaint may not win back his graces, if you’re getting nowhere, do you really want to stay in a situation like this anyway? You do have rights and if you feel genuinely harmed (and can back it up) fight for those rights.

Favoritism – If your boss has a favorite and it’s not you, this can also be difficult. This doesn’t just affect you but the entire company. Gain the support of fellow co-workers or supervisors to speak to the boss. Sayings like, “Wow didn’t John just get those sports event tickets last time?” may work but you’re better off simply asking for the tickets yourself. While you may not agree with this, I promise you a boss with favorites will see their mistake when perks are spaced out—and they’ll realize it fast.

Outrageous Requests – I once had a boss that asked me not only to pick up his dry cleaning, I also had to drive him to pick up his cocaine (no kidding) and he requested I use my credit card to order flowers for his girlfriend—yep he was married. Once you agree to do anything you feel is illegal or not in your job description, you’ll be expected to continue. When asked to do something you feel is an unfair request, politely decline and tell the boss you don’t feel comfortable completing the task. Believe me, they’ll back off.

Should You Throw in the Towel?

Throw in the towel

A recent National Public Radio (NPR) poll on mean bosses said people thought of their bosses as “control freaks, stress monkeys and corporate narcissists.” If you simply can’t please your boss and even if you confront a mean boss and nothing changes, is it really worth your valuable time?

A person spends a large amount of their lifetime on the job and if your job is a miserable experience no matter how hard you try, perhaps it’s time to move on. Weigh the pros and cons and you’ll likely find the cons outweigh the pros.

There’s no reason you can’t search for a job while you’re currently employed—just don’t use the company computer to write or email your resume to prospective employers.

Finally, I recommend, if you possibly can, asking for an exit interview when you determine it’s time to leave. It may not change your situation but it may make a difference to those who follow you.



Jean Scheid has been a business owner for over 17 years and holds a degree in human resources.

Image Credits:

Argue - MorgueFile/mzacha

Donald Trump - Wikimedia Commons/Gage Skidmore

Crazy Eyes - MorgueFile/Alvinmann

Towel - MorgueFile/agathabrown